CH660005A5 - N-oxid-pyridylcarbonsaeureester. - Google Patents
N-oxid-pyridylcarbonsaeureester. Download PDFInfo
- Publication number
- CH660005A5 CH660005A5 CH2092/84A CH209284A CH660005A5 CH 660005 A5 CH660005 A5 CH 660005A5 CH 2092/84 A CH2092/84 A CH 2092/84A CH 209284 A CH209284 A CH 209284A CH 660005 A5 CH660005 A5 CH 660005A5
- Authority
- CH
- Switzerland
- Prior art keywords
- oxide
- alkyl
- branched
- cycloalkyl
- straight
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 N-oxide pyridyl carboxylic acid esters Chemical class 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- LRKQCBDEEINFNM-UHFFFAOYSA-N (2-cyclohexylphenyl) 1-oxidopyridin-1-ium-3-carboxylate Chemical group [O-][N+]1=CC=CC(C(=O)OC=2C(=CC=CC=2)C2CCCCC2)=C1 LRKQCBDEEINFNM-UHFFFAOYSA-N 0.000 claims 1
- IKARRQFFZRTPEB-UHFFFAOYSA-N (2-tert-butyl-4-cyclohexylphenyl) pyridine-3-carboxylate Chemical compound CC(C)(C)C1=CC(C2CCCCC2)=CC=C1OC(=O)C1=CC=CN=C1 IKARRQFFZRTPEB-UHFFFAOYSA-N 0.000 claims 1
- WZPVEPWPLQMODU-UHFFFAOYSA-N (4-cyclohexylphenyl) pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C=C1)=CC=C1C1CCCCC1 WZPVEPWPLQMODU-UHFFFAOYSA-N 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 claims 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 30
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 235000012000 cholesterol Nutrition 0.000 description 12
- 235000001968 nicotinic acid Nutrition 0.000 description 10
- 239000011664 nicotinic acid Substances 0.000 description 9
- 210000004185 liver Anatomy 0.000 description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 8
- 229960003512 nicotinic acid Drugs 0.000 description 7
- 201000001320 Atherosclerosis Diseases 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 108010010234 HDL Lipoproteins Proteins 0.000 description 4
- 102000015779 HDL Lipoproteins Human genes 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- 210000002824 peroxisome Anatomy 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010028554 LDL Cholesterol Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000006053 animal diet Substances 0.000 description 2
- 230000001315 anti-hyperlipaemic effect Effects 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 230000000923 atherogenic effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000007505 plaque formation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KSTIXPJVWUSZJG-UHFFFAOYSA-N 1-oxido-2-phenylpyridin-1-ium-3-carboxylic acid Chemical compound C1=CC=C(C=C1)C2=C(C=CC=[N+]2[O-])C(=O)O KSTIXPJVWUSZJG-UHFFFAOYSA-N 0.000 description 1
- IGZUQUCLEJITAB-UHFFFAOYSA-N 2-(2-cyclohexylphenyl)-1-oxidopyridin-1-ium-3-carboxylic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1C1=CC=CC=C1C1CCCCC1 IGZUQUCLEJITAB-UHFFFAOYSA-N 0.000 description 1
- OUZWJTGVKVJSFA-UHFFFAOYSA-N 2-(2-tert-butyl-4-cyclohexylphenyl)-1-oxidopyridin-1-ium-3-carboxylic acid Chemical compound CC(C)(C)C1=CC(C2CCCCC2)=CC=C1C1=C(C(O)=O)C=CC=[N+]1[O-] OUZWJTGVKVJSFA-UHFFFAOYSA-N 0.000 description 1
- DESCEKJWVVRAQC-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)-1-oxidopyridin-1-ium-3-carboxylic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1C1=CC=C(C2CCCCC2)C=C1 DESCEKJWVVRAQC-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 206010016825 Flushing Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000042032 Petrocephalus catostoma Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- FVTRDWMTAVVDCU-UHFFFAOYSA-N acetic acid;hydrogen peroxide Chemical compound OO.CC(O)=O FVTRDWMTAVVDCU-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000036523 atherogenesis Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 229960003545 benzarone Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001855 preneoplastic effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003815 prostacyclins Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000002666 vasoprotective effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833315877 DE3315877A1 (de) | 1983-05-02 | 1983-05-02 | N-oxide von pyridyl-carbonsaeureestern, ein verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH660005A5 true CH660005A5 (de) | 1987-03-13 |
Family
ID=6197884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2092/84A CH660005A5 (de) | 1983-05-02 | 1984-04-26 | N-oxid-pyridylcarbonsaeureester. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4758581A (xx) |
| JP (1) | JPS59206357A (xx) |
| KR (1) | KR860001907B1 (xx) |
| AU (1) | AU564780B2 (xx) |
| BE (1) | BE899558A (xx) |
| CA (1) | CA1247092A (xx) |
| CH (1) | CH660005A5 (xx) |
| CS (1) | CS241082B2 (xx) |
| DE (1) | DE3315877A1 (xx) |
| DK (1) | DK159105C (xx) |
| ES (1) | ES532079A0 (xx) |
| FI (1) | FI80444C (xx) |
| FR (1) | FR2545486B1 (xx) |
| GB (1) | GB2139621B (xx) |
| GR (1) | GR79862B (xx) |
| HU (1) | HU191681B (xx) |
| IE (1) | IE57393B1 (xx) |
| IL (1) | IL71734A (xx) |
| IT (1) | IT1206144B (xx) |
| LU (1) | LU85344A1 (xx) |
| NL (1) | NL8401357A (xx) |
| SE (1) | SE454986B (xx) |
| YU (1) | YU45900B (xx) |
| ZA (1) | ZA843278B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6129930A (en) | 1993-09-20 | 2000-10-10 | Bova; David J. | Methods and sustained release nicotinic acid compositions for treating hyperlipidemia at night |
| US6818229B1 (en) | 1993-09-20 | 2004-11-16 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia |
| US6080428A (en) | 1993-09-20 | 2000-06-27 | Bova; David J. | Nicotinic acid compositions for treating hyperlipidemia and related methods therefor |
| US6746691B2 (en) | 1993-09-20 | 2004-06-08 | Kos Pharmaceuticals, Inc. | Intermediate release nicotinic acid compositions for treating hyperlipidemia having unique biopharmaceutical characteristics |
| US6676967B1 (en) | 1993-09-20 | 2004-01-13 | Kos Pharmaceuticals, Inc. | Methods for reducing flushing in individuals being treated with nicotinic acid for hyperlipidemia |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT291853B (de) * | 1967-03-22 | 1971-08-10 | Buero Patent Ag | Automatische, gleislose Förderanlage |
| GB2193359A (en) * | 1986-07-31 | 1988-02-03 | Multitone Electronics Plc | Area communication systems |
| US4797656A (en) * | 1987-01-28 | 1989-01-10 | Keppler Charles N | Appliance paging system |
| EP0386411A1 (en) * | 1989-02-09 | 1990-09-12 | Motorola, Inc. | Paging by text matching |
| US5012749A (en) * | 1988-12-27 | 1991-05-07 | The Allen Group Inc. | Radio controlled material handling apparatus |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1256M (fr) * | 1961-06-26 | 1962-04-16 | M I P Soc Amilloise De Prod Ch | Médicament hypocholésterolémiant a base de n-oxyde de l'acide nicotinique. |
| GB1213162A (en) * | 1966-11-16 | 1970-11-18 | Astra Ab | Serum lipid lowering pyridine derivatives and their preparation |
| DE3009099A1 (de) * | 1980-03-10 | 1981-09-17 | Merz + Co GmbH & Co, 6000 Frankfurt | Neue phenylester der nikotinsaeure und verfahren zu ihrer herstellung |
| US4321268A (en) * | 1979-02-08 | 1982-03-23 | Merz & Co. | Certain substituted phenyl esters of nicotinic acid, compositions and methods of using same |
-
1983
- 1983-05-02 DE DE19833315877 patent/DE3315877A1/de active Granted
-
1984
- 1984-04-26 YU YU74384A patent/YU45900B/sh unknown
- 1984-04-26 CH CH2092/84A patent/CH660005A5/de not_active IP Right Cessation
- 1984-04-26 SE SE8402297A patent/SE454986B/sv not_active IP Right Cessation
- 1984-04-27 NL NL8401357A patent/NL8401357A/nl not_active Application Discontinuation
- 1984-04-28 HU HU841684A patent/HU191681B/hu not_active IP Right Cessation
- 1984-04-30 ES ES532079A patent/ES532079A0/es active Granted
- 1984-04-30 GR GR74551A patent/GR79862B/el unknown
- 1984-04-30 KR KR1019840002323A patent/KR860001907B1/ko not_active IP Right Cessation
- 1984-05-01 GB GB08411081A patent/GB2139621B/en not_active Expired
- 1984-05-01 DK DK216484A patent/DK159105C/da not_active IP Right Cessation
- 1984-05-01 CA CA000453248A patent/CA1247092A/en not_active Expired
- 1984-05-01 IE IE1074/84A patent/IE57393B1/en not_active IP Right Cessation
- 1984-05-02 IL IL71734A patent/IL71734A/xx unknown
- 1984-05-02 BE BE0/212858A patent/BE899558A/fr not_active IP Right Cessation
- 1984-05-02 LU LU85344A patent/LU85344A1/fr unknown
- 1984-05-02 AU AU27604/84A patent/AU564780B2/en not_active Ceased
- 1984-05-02 JP JP59087963A patent/JPS59206357A/ja active Granted
- 1984-05-02 CS CS843252A patent/CS241082B2/cs unknown
- 1984-05-02 FR FR8406845A patent/FR2545486B1/fr not_active Expired
- 1984-05-02 ZA ZA843278A patent/ZA843278B/xx unknown
- 1984-05-02 FI FI841736A patent/FI80444C/fi not_active IP Right Cessation
- 1984-05-02 IT IT8420763A patent/IT1206144B/it active
-
1987
- 1987-09-29 US US07/102,025 patent/US4758581A/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT291853B (de) * | 1967-03-22 | 1971-08-10 | Buero Patent Ag | Automatische, gleislose Förderanlage |
| GB2193359A (en) * | 1986-07-31 | 1988-02-03 | Multitone Electronics Plc | Area communication systems |
| US4797656A (en) * | 1987-01-28 | 1989-01-10 | Keppler Charles N | Appliance paging system |
| US5012749A (en) * | 1988-12-27 | 1991-05-07 | The Allen Group Inc. | Radio controlled material handling apparatus |
| EP0386411A1 (en) * | 1989-02-09 | 1990-09-12 | Motorola, Inc. | Paging by text matching |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |